Light rosin ester compositions and methods of making same

Patent metadata

Field	Value
Publication number	US-2019002733-A1
Application number	US-201816024794-A
Country	US
Kind code	A1
Filing date	Jun 30, 2018
Priority date	Jun 30, 2017
Publication date	Jan 3, 2019
Grant date	—

Abstract

A light color or a low color rosin or a rosin ester composition is disclosed. Significant color improvement can be obtained for a low color rosin, or a rosin ester by using a co-catalyst. In one embodiment, the co-catalyst has a triplet formation quantum yield (ϕ T ) of greater than 0.5 and a triplet lifetime (τ T ) of greater than 0.5 microseconds In another embodiment, the co-catalyst is selected from acridone, anthrone, 9-fluorenone, thioxanthone, xanthone, derivatives and combinations thereof.

First claim

1 . A method for producing a light color rosin comprising:
contacting one or more rosins with a co-catalyst to produce a mixture; heating the mixture to a temperature to produce a light color rosin; wherein the co-catalyst comprises compounds represented by formula:

wherein n=0, 1 or 2;
X represents oxygen, sulphur, nitrogen, or carbon;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 and Z 8 are the same or different and each represents carbon or nitrogen;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and each is independently selected from the group of hydrogen, an alkyl group, an aryl group, an arylalkyl, an alkenyl group, an arylalkenyl group, an alkynyl group, an arylalkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkylene group, a cycloalkylalkylene group, an alkynylene group, a phenyl group, a tolyl group, a naphtyl group, a pyridyl group, a furyl group, an acyl group, a propionyl group, a formyl group, a benzoyl group, a acetoxy group, a halogen, an alkoxy group, an amino group, a benzyl, halogen substituted benzyl group, a alkyl substituted benzyl group, a alkoxy substituted benzyl group, a halogen substituted aryl group, an alkyl substituted aryl group, an alkoxy substituted aryl group, a dialkylamino group, a monoalkylamino group, a monoalkylamido group, a dialkylamido group, a cyano group, a hydroxymethyl group, a hydroxyalkyl group, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfonyl group, a nitro group, a carboxyl group, a hydroxyl group, an alkoxyalkyl group, an aryloxyalkyl group, a sulfamoyl group, a dimethylsulfamido group, a sulfhydryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfanyl group, an arylsulfanyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, a carbamoyl group, a carbonyl chloride group, a phosphine group, a phosphate group, a phosphodiester group, a phosphonic acid group, an oxiranylalkyl group, a carboxyalkyl group, a carboxyalkyl group, a glucopyranosyl group, and a glucopyranosyloxy group.

2 . The method of claim 1 , wherein the co-catalyst has a triplet formation quantum yield (ϕ T ) of greater than 0.5 and a triplet lifetime (τ T ) of greater than 0.5 microseconds.

3 . The method of claim 1 , wherein the co-catalyst comprises at least one of acridone, anthrone, 9-fluorenone, thioxanthone, xanthone, derivatives, and combinations thereof.

4 . The method of claim 1 for producing a light color rosin, wherein the light color rosin has an initial (neat) Gardner color, as determined according to ASTM D1544-04 (2010), of less than 10.

5 . The method of claim 1 , further comprising contacting the mixture with a disproportionation catalyst.

6 . The method of claim 5 , wherein the disproportionation catalyst is selected from the group of 2,2′thiobisphenols, 3,3′-thiobisphenols, 4,4′-thiobis(resorcinol), 1,1′-thiobis(pyrogallol), 4,4′-thiobis(6-t-butyl-m-cresol), 4,4′-thiobis(6-t-butyl-o-cresol) thiobisnaphthols, 2,2′-thio-bisphenols, 3,3′-thio-bis phenols, palladium, nickel, platinum, iodines, iodides, sulfides, poly-t-butylphenoldisulfide, 4,4′thiobis(2-t-butyl-5-methylphenol, nonylphenol disulfide oligomers, amylphenol disulfide polymer, and combinations thereof.

7 . The method of claim 5 , wherein the disproportionation catalyst is present in an amount of from 0.01 wt. % to 5.0 wt. %, and the co-catalyst is present in an amount of from 0.01 wt. % to 5.0 wt. %, based on the total weight of the rosin or rosin ester.

8 . The method of claim 1 for producing a light color rosin, wherein the one or more rosins comprise any of a tall oil rosin, a gum rosin, a wood rosin, a disproportionated rosin, a fortified rosin and combinations thereof.

9 . The method of claim 1 for producing a light color rosin, wherein the one or more rosins have an acid number value ranging from about 120 mg KOH/gram to about 190 mg KOH/gram.

10 . A method for producing a light color rosin ester, the method comprising:
contacting one or more rosins with a co-catalyst, one or more polyhydric alcohols, optionally one or more of a monocarboxylic acid, and optionally one or more of a polycarboxylic acid to produce a mixture; heating the mixture to a temperature to produce a light color rosin ester; wherein the co-catalyst comprises compounds represented by formula:

wherein n=0, 1 or 2;
X represents oxygen, sulphur, nitrogen, or carbon;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 and Z 8 are the same or different and each represents carbon or nitrogen;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and each is independently selected from the group of hydrogen, an alkyl group, an aryl group, an arylalkyl, an alkenyl group, an arylalkenyl group, an alkynyl group, an arylalkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkylene group, a cycloalkylalkylene group, an alkynylene group, a phenyl group, a tolyl group, a naphtyl group, a pyridyl group, a furyl group, an acyl group, a propionyl group, a formyl group, a benzoyl group, a acetoxy group, a halogen, an alkoxy group, an amino group, a benzyl, halogen substituted benzyl group, a alkyl substituted benzyl group, a alkoxy substituted benzyl group, a halogen substituted aryl group, an alkyl substituted aryl group, an alkoxy substituted aryl group, a dialkylamino group, a monoalkylamino group, a monoalkylamido group, a dialkylamido group, a cyano group, a hydroxymethyl group, a hydroxyalkyl group, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfonyl group, a nitro group, a carboxyl group, a hydroxyl group, an alkoxyalkyl group, an aryloxyalkyl group, a sulfamoyl group, a dimethylsulfamido group, a sulfhydryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfanyl group, an arylsulfanyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, a carbamoyl group, a carbonyl chloride group, a phosphine group, a phosphate group, a phosphodiester group, a phosphonic acid group, an oxiranylalkyl group, a carboxyalkyl group, a carboxyalkyl group, a glucopyranosyl group and a glucopyranosyloxy group.

11 . The method of claim 10 , further comprising contacting the mixture with a disproportionation agent.

12 . The method of claim 10 , wherein the disproportionation catalyst is selected from the group of 2,2′thiobisphenols, 3,3′-thiobisphenols, 4,4′-thiobis(resorcinol), 1,1′-thiobis(pyrogallol), 4,4′-thiobis(6-t-butyl-m-cresol), 4,4′-thiobis(6-t-butyl-o-cresol) thiobisnaphthols, 2,2′-thio-bisphenols, 3,3′-thio-bis phenols; metals, including palladium, nickel, and platinum; iodine or iodides (e.g., iron iodide); sulfides, poly-t-butylphenoldisulfide, 4,4′thiobis(2-t-butyl-5-methylphenol, nonylphenol disulfide oligomers, amylphenol disulfide polymer and combinations thereof.

13 . The method of claim 10 for producing a light color rosin ester, wherein the one or more rosins are selected from the group of a tall oil rosin, a gum rosin, a wood rosin, a disproportionated rosin, a fortified rosin, and combinations thereof.

14 . The method of claim 10 , further comprising fortifying the rosin with any of fumaric acid, maleic acid, acrylic acid, maleic anhydride, citraconic acid, mesaconic acid, itaconic acid,

Assignees

• Kraton Polymers Llc

Inventors

• Schaapman Mark C

Classifications

• C09F1/04 Primary

  Chemical modification, e.g. esterification (resin soaps C11D) · CPC title

• C08L93/04

  Rosin · CPC title

• C09F1/02

  Purification · CPC title

• C09J193/04 Primary

  Rosin · CPC title